C-H Hydroxylation Using a Heterocyclic Catalyst and Aqueous H2O2

被引：111

作者：

Litvinas, Nichole D. ^{[1
]}

Brodsky, Benjamin H. ^{[1
]}

Du Bois, J. ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 25期

基金：

美国国家科学基金会;

关键词：

benzoxathiazines; C-H hydroxylation; hydrogen peroxide; organocatalysis; oxaziridines; ASYMMETRIC EPOXIDATION; TRANSITION-STATE; IRON OXYGENASES; BONDS; OXIDATION; SELECTIVITY; OXAZIRIDINES; HYDROCARBONS; MILD;

D O I：

10.1002/anie.200901353

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Substituted benzoxathiazines function as catalysts for the selective hydroxylation of tertiary C-H bonds. Mechanistic studies have revealed an unanticipated disparity between oxaziridine reactivity and catalyst performance and have given way to a new catalyst and an aqueous H2O2 reaction protocol that greatly facilitate such transformations (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：4513 / 4516

页数：4

相关论文

共 35 条

[1] Synthetic applications of nonmetal catalysts for homogeneous oxidations [J].

Adam, W ;

Saha-Möller, CR ;

Ganeshpure, PA .

CHEMICAL REVIEWS, 2001, 101 (11) :3499-3548

[2]

Adam W, 2000, STRUCT BOND, V97, P237

[3] MECHANISM OF OXYGEN ATOM TRANSFER FROM OXAZIRIDINE TO A LITHIUM ENOLATE - A THEORETICAL-STUDY [J].

BACH, RD ;

ANDRES, JL ;

DAVIS, FA .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :613-618

[4] Cytochromes P450 as versatile biocatalysts [J].

Bernhardt, Rita .

JOURNAL OF BIOTECHNOLOGY, 2006, 124 (01) :128-145

[5] Oxaziridinium salts as hydrophobic epoxidation reagents: Remarkable hydrophobically-directed selectivity in olefin epoxidation [J].

Biscoe, MR ;

Breslow, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (31) :10812-10813

[6] An artificial cytochrome P450 that hydroxylates unactivated carbons with regio- and stereoselectivity and useful catalytic turnovers [J].

Breslow, R ;

Huang, Y ;

Zhang, XJ ;

Yang, J .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (21) :11156-11158

[7] Oxaziridine-mediated catalytic hydroxylation of unactivated 3° C-H bonds using hydrogen peroxide [J].

Brodsky, BH ;

Du Bois, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15391-15393

[8] 1,3-diol synthesis via controlled, radical-mediated C-H functionalization [J].

Chen, Ke ;

Richter, Jeremy M. ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7247-+

[9] A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis [J].

Chen, Mark S. ;

White, M. Christina .

SCIENCE, 2007, 318 (5851) :783-787

[10] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

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